Intramolecular cyclization reactions of aziridines with π-nucleophiles

被引：30

作者：

Bergmeier, SC ^{[1
]}

Katz, SJ ^{[1
]}

Huang, JF ^{[1
]}

McPherson, H ^{[1
]}

Donoghue, PJ ^{[1
]}

Reed, DD ^{[1
]}

机构：

[1] Ohio Univ, Dept Chem & Biochem, Athens, OH 45701 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 26期

基金：

美国国家科学基金会;

关键词：

aziridines; amines; bicyclic heterocyclic compounds;

D O I：

10.1016/j.tetlet.2004.05.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have found that aziridines will react with a variety of pi-nucleophiles in intramolecular cyclization reactions to produce nitrogen containing core structures found in a variety of bioactive molecules. These cyclizations are more general and facile than corresponding intermolecular reactions. We have examined the effects of ring size, pi-nucleophile identity and substitution on this reaction. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5011 / 5014

页数：4

共 33 条

[1] SYNTHESIS OF (+/-)-KARAHANA ETHER AND A (+/-)-LABDADIENOIC ACID BY THE ELECTROPHILIC CYCLIZATION OF EPOXY ALLYLSILANES [J].

ARMSTRONG, RJ ;

WEILER, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (03) :584-596

[2]

Bennani YL, 1998, SYNLETT, P754

[3] Synthesis of bicyclic proline analogs using a formal [3+2] intramolecular aziridine-allylsilane cycloaddition reaction [J].

Bergmeier, SC ;

Fundy, SL ;

Seth, PP .

TETRAHEDRON, 1999, 55 (26) :8025-8038

[4] THE SYNTHESIS OF GAMMA-AMINO OLEFINS - A NOVEL INTRAMOLECULAR AZIRIDINE - ALLYLSILANE REACTION [J].

BERGMEIER, SC ;

SETH, PP .

TETRAHEDRON LETTERS, 1995, 36 (22) :3793-3796

[5] Aziridine-allylsilane-mediated total synthesis of (-)-yohimbane [J].

Bergmeier, SC ;

Seth, PP .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3237-3243

[6] A tandem Horner-Emmons olefination-conjugate addition approach to the synthesis of 1,5-disubstituted-6-azabicyclo[3.2.1]octanes based on the AE ring structure of the norditerpenoid alkaloid methyllycaconitine [J].

Callis, DJ ;

Thomas, NF ;

Pearson, DPJ ;

Potter, BVL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4634-4640

[7] APHANORPHINE, A NOVEL TRICYCLIC ALKALOID FROM THE BLUE-GREEN-ALGA APHANIZOMENON-FLOS-AQUAE [J].

GULAVITA, N ;

HORI, A ;

SHIMIZU, Y ;

LASZLO, P ;

CLARDY, J .

TETRAHEDRON LETTERS, 1988, 29 (35) :4381-4384

[8] Stereo-random synthesis of highly functionalized proline analogues by azomethine cycloaddition [J].

Henkel, B ;

Stenzel, W ;

Schotten, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (09) :975-977

[9] ABSOLUTE STEREOCHEMISTRY OF SECURININE [J].

HORII, Z ;

YAMAWAKI, Y ;

SAITO, S ;

TAMURA, Y ;

KODERA, K ;

IKEDA, M .

TETRAHEDRON, 1963, 19 (12) :2101-&

[10] AZA-PAYNE REARRANGEMENT OF ACTIVATED 2-AZIRIDINEMETHANOLS AND 2,3-EPOXY AMINES UNDER BASIC CONDITIONS [J].

IBUKA, T ;

NAKAI, K ;

HABASHITA, H ;

HOTTA, Y ;

TAMAMURA, H ;

FUJII, N ;

MIMURA, N ;

MIWA, Y ;

TAGA, T ;

CHOUNAN, Y ;

YAMAMOTO, Y ;

OTAKA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2044-2058

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